18099-96-2

Basic information

• Product Name: 1,2-Naphthalenedione, 4-bromo-
• CAS NO: 18099-96-2
• Molecular Formula: C10H5BrO2
• Molecular Weight: 237.052
• Mol File: 18099-96-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1,2-Naphthalenedione, 4-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Naphthalenedione, 4-bromo-(18099-96-2)
• EPA Substance Registry System: 1,2-Naphthalenedione, 4-bromo-(18099-96-2)

Safety Data

• Hazardous Substances Data: 18099-96-2(Hazardous Substances Data)

Upstream product

• 571-57-3 4-bromo-1-naphthol 
• 90-11-9 1-Bromonaphthalene 

Downstream Products

• 10035-10-6 hydrogen bromide 
• 73671-07-5 4-phenylnaphthalene-1,2-dione 
• 27828-56-4 4-(phenylamino)naphthalene-1,2-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 

Relevant articles and documents

Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents

Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.